Hydrochloric Acid → N-[4-Methoxy-3-(1-propyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxybenzenesulfonamide

HRID 238975Notes

Reaction equation

HRID 238975 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=2)(=[O:12])=[O:11])=[CH:5][C:4]=1[CH:24]1[CH2:28][CH2:27][N:26]([C:29](=O)[CH2:30][CH3:31])[CH2:25]1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:22])([F:23])[F:21])[CH:14]=2)(=[O:12])=[O:11])=[CH:5][C:4]=1[CH:24]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH3:31])[CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68953299N-[4-Methoxy-3-(1-propionyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxybenzenesulfonamide

Product 1

HCID 68950150N-[4-Methoxy-3-(1-propyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxybenzenesulfonamideYield 0%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[4-Methoxy-3-(1-propionyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzenesulfonamide (0.19 g, 0.4 mmol) were dissolved in 15 ml tetrahydrofurane and 2 ml 1 M boranetetrahydrofuran complex in tetrahydrofurane was added dropwise. The reaction mixture was heated to reflux for 30 minutes, 2 ml of 2 N aqueous hydrochloric acid was added and the mixture was refluxed again for 3 h. After stirring for 16 h at room temperature, the solvent was evaporated, the residue was treated with water and the pH was adjusted to alkaline pH with 1 N aqueous NaOH. The aqueous layer was extracted twice with diethylether, the combined organic layers were dried over magnesium sulfate, filtered and the solvent was evaporated. The crude product was chromatographed on a chromabond column using 0-5% dichloromethane/methanol as eluent, to yield 0.077 mg of the title compound.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 30 minutes
  4. temperaturethe mixture was refluxed again for 3 h
  5. customthe solvent was evaporated
  6. additionthe residue was treated with water
  7. extractionThe aqueous layer was extracted twice with diethylether
  8. dry with materialthe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe crude product was chromatographed on a chromabond column

Sources & evidence

ORD record
ord-1dc170bff3144f1ea4003f04bc26af09
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

Loading…